2006 AIChE Annual Meeting

(175f) Solid Acid Porous Catalysts for the Transformation of 1-Adamantanol

Authors

Elangovan, S. P. - Presenter, The University of Tokyo
Inoue, K., The University of Tokyo
Okubo, T., The University Of Tokyo
Kojima, A., Idemitsu Petrochemical Co. Ltd
Ogura, M., The University of Tokyo
Abstract

Catalytic transformation of 1-Adamantanol has been carried out over microporous materials viz. Zeolite-Y, USY, Beta, Mordenite, SAPO-8, SAPO-5, and CoAPO-5 whose pore size is close to the kinetic diameter of the reactant and product molecules. In presence of chloroacetic acid solvent, 1-adamantanol (1-Adol) forms 1-adamantylacetate (1-Adoac) and equilibrium is established between 1-Adol and formed 1-Adoac thereby reduces polymerization of 1-Adol to some extent. The products formed are 2-Adamantane derivatives (2-Derivatives) viz., 2-Adamantanol (2-Adol), 2-Adamantanone (2-Ado) and 2-Adamantane acetate (2-Adoac) which serve as important intermediates for a variety of pharmaceuticals and functional materials, along with adamantane and some of polymerized products. 2-Ado is produced via disproportionation of 1-Adol and formed 2-Adol attributed to an intermolecular hydride transfer reaction over solid acid catalysts. Acidity plays an important role in producing 2-Derivatives selectively. Influence of pore size on the transformation of 1-adamantanol has also been discussed. A new experimental strategy along with addition of adamantane with the reactant, reduces the formation of least preferred adamantane from 1-Adol, and in turn, increases the selective formation of more favored 2-Derivatives. The formation of products through a different route has been completely explained with the assistance of a detailed reaction mechanism.